I was recently wondering the same thing, but I didn't find any easy answer. 
I ended up creating an extension that sends a ping to healthchecks.io with 
every archive interval. That way, you can get an email, text message, 
whatever if weewx stops reporting. 
On Tuesday, March 12, 2019 at 9:29:41 PM UTC-4 [email protected] wrote:

> It comes down to the source of the failure you want to monitor.
> Using systemd will let you restart weewx if it stops running  but will not 
> detect it looping or otherwise 'working' (as seen by the OS). It also won't 
> detect a OS crash or power down.
> if you just want the appearance of a file or data records etc. on some 
> external computer (whether inside or outside your LAN) then you could set 
> up something like an MQTT broker and have an app that subscribes tot he 
> packets and does whatever you want if something is not received - a bit 
> like a 'heartbeat monitor' app. However this would show you an error if 
> anything between weewx and the subscriber was not working, not weewx 
> specifically.
> Susan
>

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